7-(Benzyloxy)isoquinoline → 7-(Benzyloxy)-1,2,3,4-tetrahydroisoquinoline

HRID 1940568Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1940568
[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([CH:13]=[CH:14][N:15]=[CH:16]2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>CO.[Pt]=O>[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([CH2:13][CH2:14][NH:15][CH2:16]2)=[CH:11][CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

4

Edukt 1

HCID 211924457-(Benzyloxy)isoquinoline

Produkt 1

HCID 214630147-(Benzyloxy)-1,2,3,4-tetrahydroisoquinolineAusbeute 64 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 82844Platinum oxide (PtO)KatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

7-Benzyloxyisoquinoline (1.5 g, 6.37 mmol) in methanol (100 ml) was hydrogenated at 50 psi on a Parr apparatus using platinum oxide (100 mg) as catalyst. The catalyst was collected by filtration, the filtrate evaporated under reduced pressure to give an oil which crystallised on treatment with hexane/diethyl ether to give the title compound (0.96 g, 64%); δH (CDCl3) 2.72 (2H, t, J 6 Hz, CH2), 3.11 (2H, t, J 6 Hz, CH2), 3.90 (2H, s, CH2), 6.62 (1H, d, J 2.25 Hz, tetrahydroisoquinolinyl H), 6.78 (1H, dd, J 5.75, 2.75 Hz, tetrahydroisoquinolinyl H), 6.99 (1H, d, J 9.25 Hz, tetrahydroisoquinolinyl H), and 7.25-7.43 (5H, m, ArH).

Aufarbeitung

  1. filtrationThe catalyst was collected by filtration
  2. customthe filtrate evaporated under reduced pressure
  3. customto give an oil which
  4. customcrystallised on treatment with hexane/diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-3201db18bb334fb4a3e432ad9fa7efd5
Quelldatensatz
uspto-grants-1997_12
Patentnummer
US05700809

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